Substituted piperazine

Substituted piperazines are a class of chemical compounds based on a piperazine core.^[1] Some are used as recreational drugs and some are used in scientific research.^[2]

List of substituted piperazines

Benzylpiperazines

See also: Benzylpiperazine § Chemical derivatives

•  
  1-Benzylpiperazine (BZP)
•  
  1-Methyl-4-benzylpiperazine (MBZP)
•  
  1,4-Dibenzylpiperazine (DBZP)
•  
  3,4-Methylenedioxy-1-benzylpiperazine (MDBZP)
•  
  4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP)
•  
  Methoxypiperamide (MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone)
•  
  Sunifiram (1-benzoyl-4-propanoylpiperazine)
•  
  3-Methylbenzylpiperazine (3-MeBZP)
•  
  Befuraline
  (also produces benzylpiperazine as a metabolite)
•  
  Fipexide
  (also produces substituted benzylpiperazine as a metabolite)
•  
  Piberaline
  (also produces benzylpiperazine as a metabolite)

Phenylpiperazines

See also: Phenylpiperazine

ortho-Substituted

• 2-Chlorophenylpiperazine (oCPP)
• 2-Methylphenylpiperazine (oMPP)
• 2-Methoxyphenylpiperazine (oMeOPP)
• Vortioxetine

Enpiprazole is known to produce oCPP as a metabolite.

Enciprazine was initially anticipated to produce oMeOPP as a metabolite, but this turned out not to be the case.

meta-Substituted

• 3-Chlorophenylpiperazine (mCPP)
• 3-Methoxyphenylpiperazine (mMeOPP)
• 3-Trifluoromethylphenylpiperazine (TFMPP)
• 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP)

Trazodone, nefazodone, mepiprazole, and others produce mCPP as a metabolite.

para-Substituted

• 4-Chlorophenylpiperazine (pCPP)
• 4-Fluorophenylpiperazine (pFPP)
• 4-Methylphenylpiperazine (pMPP)
• 4-Methoxyphenylpiperazine (MeOPP)
• 4-Nitrophenylpiperazine (pNPP)
• 4-Trifluoromethylphenylpiperazine (pTFMPP)

Multiple substitutions

•  
  2,3-Dichlorophenylpiperazine (2,3-DCPP)
•  
  3,4-Dichlorophenylpiperazine (3,4-DCPP)

• 2,3-Methylphenylpiperazine (DMPP)
• 3-Trifluoromethyl-4-chlorophenylpiperazine (TFMCPP)

Others

• 1-Phenylpiperazine (PP)

Other arylpiperazines

• 1-(1-Naphthyl)piperazine (1-NP)
• 1-(2-Pyrimidinyl)piperazine (1-PP)
• ORG-12962 (1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine)
• Quipazine (2-piperazin-1-ylquinoline)

Many azapirones such as buspirone, gepirone, and tandospirone produce 1-PP as a metabolite.

See also

• Substituted α-alkyltryptamine
• Substituted amphetamine
• Substituted cathinone
• Substituted methylenedioxyphenethylamine
• Substituted phenethylamine
• Substituted phenylmorpholine
• Substituted tryptamine

References

1. Laras, Y.; Garino, C.; Dessolin, J.; Weck, C.; Moret, V.; Rolland, A.; Kraus, J.-L. (2009-02-01). "New N4-substituted piperazine naphthamide derivatives as BACE-1 inhibitors". Journal of Enzyme Inhibition and Medicinal Chemistry. 24 (1): 181–187. doi:10.1080/14756360802048939. ISSN 1475-6366. PMID 18770069. S2CID 85385527.
2. Alghamdi, Saad; Alshehri, Mohammed M.; Asif, Mohammad (2022). "The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review". Mini-Reviews in Organic Chemistry. 19 (7): 798–810. doi:10.2174/1570193x19666220119120211.